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Catalysis of nucleophilic aromatic substitutions in the 2,6,8-trisubstituted purines and application in the synthesis of combinatorial libraries

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Abstract

The following paper summarizes our work on compound libraries of 2,6,8-trisubstituted purines. This synthesis route on a polystyrene support begins with 2,6-dichloro purine making extensive use of catalysis. During the synthesis the polymer bound purines were brominated selectively on C8. The substitution reaction of C6-Cl by amines was found to be acid catalyzed. The substitution of C2-Cl by amines and aryls, as well as the substitution of a C8-Br by aryls, alkenyl and alkynyl groups can be catalyzed by transition metals. Under some bromination conditions novel selective oxidative transformations of 2-amino groups in 2,6-diamino purines have been found.

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Authors and Affiliations

  1. Pharmazentrum, der Universitaet Basel, Basel, Switzerland

    Claudia Riva-Toniolo

  2. Novartis Pharma AG, Basel, Switzerland

    Sascha Müller & Josette Schaub

  3. Pharmacia Italia S.p.A, Nerviano (Mi), Italy

    Wolfgang K.-D. Brill

Authors
  1. Claudia Riva-Toniolo
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  2. Sascha Müller
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  3. Josette Schaub
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  4. Wolfgang K.-D. Brill
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Correspondence to Wolfgang K.-D. Brill.

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Riva-Toniolo, C., Müller, S., Schaub, J. et al. Catalysis of nucleophilic aromatic substitutions in the 2,6,8-trisubstituted purines and application in the synthesis of combinatorial libraries. Mol Divers 6, 43–53 (2003). https://doi.org/10.1023/A:1024895515316

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